Acetic Anhydride → HCID 70567532, compound

HRID 2287113Notes

Reaction equation

HRID 2287113 reaction equation
[CH:1]([S:3][C@H:4]1[N:7]([C:8]([O:10][CH2:11][CH2:12][C@@H:13]([OH:15])[CH3:14])=[O:9])[C:6](=[O:16])[CH2:5]1)=[CH2:2].[C:17](OC(=O)C)(=[O:19])[CH3:18].CCN(CC)CC.C(OCC)(=O)C.C1C=CC=CC=1>C(Cl)Cl>[CH:1]([S:3][C@H:4]1[N:7]([C:8]([O:10][CH2:11][CH2:12][C@@H:13]([O:15][C:17](=[O:19])[CH3:18])[CH3:14])=[O:9])[C:6](=[O:16])[CH2:5]1)=[CH2:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21583983Benzene ethyl acetateHCID 70567759HCID 70567759, compound

Product 1

HCID 70567532HCID 70567532, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (4 R,S)-4-vinylthio-(1-hydroxyethyl-2-ethoxycarbonyl)-2-oxo-azetidine (1.01 g, 4.13 mmole), acetic anhydride (1 ml, 10.6 mmole), and Et3N (0.7 ml, 5 mmole) dissolved in methylene chloride (60 ml) was allowed to stand overnight at room temperature. The reaction mixture was then washed with brine (3 times), and dried on Na2SO4. Evaporation of the solvent left a residue which, after column chromatography (SiO2, 10% ethyl acetate-benzene), yielded 950 mg (3.31 mmole, 81%) of an oily product.

Workup

  1. washThe reaction mixture was then washed with brine (3 times)
  2. customdried on Na2SO4
  3. customEvaporation of the solvent
  4. waitleft a residue which

Sources & evidence

ORD record
ord-dd2cd102ade94376aa285f5a23a92c7b
Source dataset
uspto-grants-1981_05
Patent number
US04269771

Reaction notes

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